Al Capone's business structure kept him from ever getting charged for bootlegging

How tax laws helped the federal government catch mob bosses during Prohibition

The IRS arrested top mob bosses during Prohibition after the Supreme Court ruled illegally-made income could be taxed. The IRS's biggest catch was Al Capone, who was charged with tax evasion and sentenced to 11 years in prison. But Capone wasn't the only bootlegger the IRS nabbed for tax evasion during this era.

There's a myth that Al Capone coined the term 'money laundering'

Al Capone owned multiple dry cleaning businesses in Chicago that were believed to be a front for his extensive bootlegging empire, but that's most likely not where the term "money laundering" actually came from. The word didn't appear in popular lexicon until the 1970s, and there aren't recorded references to Al Capone as a money launderer until much later.

The federal government allowed toxic chemicals into alcohol during Prohibition

Industrial alcohol was still legal during Prohibition, and was often used by bootleggers. In an attempt to disrupt the black market, the government required toxic additives to be included in industrial alcohol, leading to more than one death.

A group of daring bootleggers created NASCAR

When Prohibition made alcohol illegal in 1920, it didn’t stop Americans from making and consuming it. The law drove the practice underground. Runners risked their lives to deliver moonshine and began racing among themselves.

The St. Valentine's Day massacre is still unsolved

On Feb. 14, 1929, several men believed to be working for Chicago gangster George "Bugs" Moran, an enemy of notorious mobster Al Capone, were killed by several gunmen dressed as police. No one was ever brought to trial for the murders.

Why ‘Shoeless Joe’ Jackson was banned from Major League Baseball

Few baseball stars are more infamous than "Shoeless Joe" Jackson, one of the game's greatest hitters. Jackson was part of the Chicago White Sox team (notoriously dubbed the "Black Sox") accused of fixing the 1919 World Series. This resource breaks down the criminal trial that investigated those allegations. Curiously, Jackson and his teammates were acquitted, but Major League Baseball commissioner Judge Kenesaw Mountain Landis still banned them from the league for life.

JP Morgan Jr. once angered the nation with his zero-dollar tax bill

In the aftermath of the Great Depression, Congress learned that Morgan and his banking partners had avoided paying any federal income tax in 1931 and 1932. By claiming their losses in the stock market, they seemingly erased what they owed.

Often dubbed the 'king of bank robbers,' George Leonidas Leslie stole an estimated $7M (equivalent to $200M today) and charged other criminals a $20K fee to evaluate their heist plans

Leslie studied architecture and used blueprints of safes and banks to execute meticulously planned bank heists across the Northeast between 1869 and 1878. Although Leslie was an infamous bank robber by night, he posed as a member of high society by day, providing critical intel on the institutions he'd rob and helping conceal his crimes. Months before his largest planned heist, where he planned to turn on his gang, Leslie's body mysteriously washed up along the Hudson River. His killer remains a mystery.

Cocainenomics

How did Pablo Escobar rise up out of the Medellin barrios to become the CEO of a $4 billion business? This immersive look at the global drug trade spawned by the notorious drug lord, who at his peak controlled 80% of the cocaine supply in the US. This deep dive includes visualizations showing how logistics of drug smuggling evolved over the years and traces the economic impact of the industry.

After her arrest, a technicality made it harder for Holiday to perform

The Cabaret Identification Card was required for all performers in New York nightclubs that served liquor. After her arrest and yearlong imprisonment, the New York Police Department revoked Billie Holiday's card, making it extremely difficult for her to earn money. The video features contemporary jazz musician Christian McBride breaking down the history of cabaret cards and how the ban affected Holiday.

How organized crime took over post-Soviet Russia

After more than seven decades of Soviet communism, the collapse of the system in the early 1990s opened a path for organized crime to take over the country's newly-privatized industries. As Vladimir Putin centralized power in the subsequent decades, he did not vanquish the mafia, but rather tamed it. This long read explores the subtle, complex ways organized crime flourishes within Putin's state.

Robber barons, the monopolistic business people of the 19th century, explained

“Robber baron” was a term used to describe 19th-century businesspeople who engaged in monopolistic business practices and didn’t face much business regulation, resulting in significant wealth.

Fugazi refused to make merchandise, but that didn't stop bootleggers

The band—formed by members of Minor Threat and Rites of Spring—was known for its innovative post-hardcore music and its high-minded ethics: They released albums themselves through the Dischord label, ensured all shows were $5 all-ages affairs, and refused to make merchandise to avoid commodifying their art. That didn’t stop bootleggers.

There's a legal loophole behind California Champagne

In the late 19th century, sparkling wine production took root in California before France began the fight to own the term “Champagne.” Many American winemakers already used it for easy recognition. The battle continued for over a century before reaching an agreement in 2005, stipulating that American sparkling wine couldn’t be labeled as Champagne unless the producer was already calling it such.

Tesla's lack of business savvy and inability to commercialize led to his obscurity

For decades, despite pioneering technologies for large-scale electrical systems and telecommunications, Nikola Tesla had been forgotten to history. Rather than monetizing his work and becoming more well known, his inventor-first mentality saw him sell off lucrative patents to fund new experiments in the short term.

Early attorneys general worked alone and often kept private law practices

The first attorneys general served as the president's chief legal advisor and represented the government before the Supreme Court—but without staff, office, or salary support, many maintained private practices to supplement their income.

Although payola was made illegal in 1960, it likely continued on the Billboard charts through the '70s

In his book “Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves,” music journalist Chris Dalla Riva argues that payola, the music industry term for undisclosed paid publicity, likely continued into the 1970s with the Billboard chart. Dalla Riva cites chart irregularities and reports about Bill Wardlow, Billboard’s then director of sales, who was a known booster for disco label Casablanca Records.

Congress banned banks from paying checking account interest for 80 years

Known as "Regulation Q," the act sought to stop bank competition for customers involving increasing interest rates in the 1930s. This competition led banks to make reckless investment decisions to pay higher interest rates. During the ban, banks competed by focusing on convenience (ATMs, branches), relying on fees, and building relationships.

Coca-Cola operates under an asset-light, divided structure

The "company" manages the brand itself, as well as its secret formula and syrup production. The capital-intensive "system" of independent bottlers, on the other hand, handles manufacturing and distribution.

The Fifth Amendment covers a wide range of legal protections for those accused of a crime

While it is widely known for the right against self-incrimination, the Fifth Amendment also protects against being charged for the same crime twice, requires grand jury indictments for serious crimes, and mandates compensation when the government takes private property for public use.

Art theft is the third-largest source of criminal revenues worldwide, thanks in part to the subjective nature of valuing a work of art.

A 1993 deal with the government exempts British Royals from paying inheritance taxes

When Queen Elizabeth II died, King Charles didn't have to pay any inheritance taxes on the money he received from his mother. That's because of a unique deal the royals made with the UK government in the 1990s, in an effort to preserve the assets of the royal family that are synonymous with the institution.

Private credit is a nonbank loan made directly to a business

Similar to private equity, private credit is part of the private markets world. Both strategies offer illiquid, privately negotiated investments for privately held companies. Unlike private equity investors, however, private credit investors typically do not take ownership stakes in the companies they invest in.

A Missouri farmer sold $140M worth of fake organic feed

Randy Constant sold nonorganic feed to other farmers, who fed it to their animals, which were then sold as organic meat. The scheme began sometime in the mid-2000s and ended after a tip, likely from one of Constant’s competitors, to the US Department of Agriculture. Constant pleaded guilty and was sentenced to 10 years in prison, but died by suicide before serving time.

Some senior Nazis fled to South America and lived for decades

Using so-called "ratlines" through Spain, Italy, and into South American countries like Argentina, many of Adolf Hitler's closest associates evaded capture after the fall of Berlin in 1945. This video details the fate of eight, including infamous doctor Josef Mengele and logistics expert Adolf Eichmann.

Why wasn't German emperor Kaiser Wilhelm punished for starting WWI?

The accusations were explosive: a head of state had not only begun an illegal war, but egged his troops on to a series of horrific atrocities that left

The idea for the Federal Reserve was conceived in secret in 1910—with bankers donning duck hunt gear for disguise while traveling to a remote country club on Georgia's Jekyll Island

US intelligence allegedly pursued more than 600 schemes to assassinate Cuban revolutionary Fidel Castro.

Despite being favored by 87% of Americans, Congress does not have term limits.

The story of Dollree Mapp, whose legal challenge over her 1957 conviction for possessing "obscene material" led to a major strengthening of the Fourth Amendment

Mark Twain spent decades feuding with the US Postal Service, convinced its costs and regulations were bureaucratic overreach.

After her fellow cult members tried to kill her with an LSD-infused hamburger, one member of the Manson Family, the murderous cult led by Charles Manson, decided to testify against the group's leader.

Abraham Lincoln was almost assassinated weeks before his inauguration as he traveled from Illinois to DC through Baltimore in 1861; it took two independent claims for Lincoln to be convinced the threat was real

Budweiser stores yeast derived from the original 1800s strain in a secret bunker, which only the Head of Yeast Management can access—not even the CEO

The identity of the Tank Man in the iconic photo from the 1989 Tiananmen Square protests remains unknown and was possibly killed.

Pure water does not conduct electricity because this flow of energy requires the movement of charged particles, and water is a neutral molecule.

A vending machine run with Anthropic's AI went out of business after it was convinced to give away items for free and sell a video game console.

Many legends about George Washington, including his supposed wooden teeth and the story of cutting down the cherry tree, lack evidence.

The US first hosted the World Cup in 1994, a tournament that lives in soccer infamy for its poor planning and the murder of Colombian player Andres Escobar, who'd accidentally scored on his own net.

Tattoos remain visible on your skin thanks to immune cells called macrophages

Venture capital is a form of funding provided to early-stage companies with high growth potential, typically in exchange for an equity (or ownership) stake

Watch a 1934 short film starring jazz legend Cab Calloway, a major figure in the Harlem Renaissance's music scene

The price of gas is a composite made up of several different factors, with the federal gas tax making up less than 20% of what drivers pay at the pump.

In 1939, baseball star Lou Gehrig delivered his inspirational 'Luckiest Man' speech after retiring due to the health condition that now bears his name.

Frank Lloyd Wright's houses are historically hard to sell because they're old, subject to local landmark commissions, and often unfashionable

SpongeBob exemplifies Aristotle's philosophy for living well because he understands that happiness doesn't come from external factors like money, recognition, or power.

Apeirophobia is an overwhelming fear of living forever, perhaps stemming from the brain's inability to conceptualize an infinite life.

Sony set the standard for cylinder-shaped batteries when it repurposed manufacturing equipment used to make rolls of magnetic recording tape.

Learn more about the history of fireworks, which dates back to an accidental invention during an alchemist's quest for information about immortality.

Scientists have struggled to pin down Ebola's natural reservoir species for decades, but the available evidence suggests that it's very likely fruit and insect-eating bats found in Africa.